Water → Phenacyl bromide

HRID 70041

Reaktionsgleichung

Reaktionsgleichung von HRID 70041
[Br:1]Br.CO[C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9](OC)[C:10]=1OC.C1(C2SC=C(C(C3C=C(OC)C(OC)=C(OC)C=3)=O)N=2)C=CC=CC=1.O>C(O)C>[Br:1][CH2:16][C:15]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:5][CH:6]=1)=[O:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 143453',4',5'-TrimethoxyacetophenoneHCID 24408BromineHCID 252274304-(3,4,5-Trimethoxybenzoyl)-2-phenylthiazole

Produkt 1

HCID 6259Phenacyl bromideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Bromine (160 mg, 1 mmol) was added dropwise to a stirred solution of an 1-(3,4,5-trimethoxyphenyl)ethanone (210 mg, 1 mmol) in ethanol (30 mL) and the solution was stirred at 0° C. for 1h and then poured into water to form a precipitate. This was recrystallized from ethanol to give bromoacetophenone (70%) and used directly for next step. A mixture of bromoacetophenone (288 mg, 1 mmol) and benzothioamide (137 mg, 1 mmol) in ethanol was refluxed for 1h. The reaction mixture was concentrated in vacuo and purified with flash column to give 2i (167 mg, 51.1%). 1H NMR (500 MHz, CDCl3) δ 8.05-8.03 (m, 2H), 7.48-7.44 (m, 3H), 7.41 (s, 1H), 7.22 (s, 2H), 3.97 (s, 6H), 3.89 (s, 3H). MS (ESI) m/z 350.1 (M+Na)+.

Aufarbeitung

  1. customto form a precipitate
  2. customThis was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c3c6592e8cb54a76ba3fa597a5c7698a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822513B2

Verknüpfte Notizen

Wird geladen…